diff --git a/Essentials/src/main/java/com/earth2me/essentials/ISettings.java b/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
index 4da7f52549b..926a23ac452 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
@@ -3,6 +3,7 @@
 import com.earth2me.essentials.commands.IEssentialsCommand;
 import com.earth2me.essentials.signs.EssentialsSign;
 import com.earth2me.essentials.textreader.IText;
+import com.earth2me.essentials.utils.NumberUtil;
 import org.bukkit.Material;
 import org.bukkit.event.EventPriority;
 import org.spongepowered.configurate.CommentedConfigurationNode;
@@ -18,6 +19,8 @@
 import java.util.regex.Pattern;
 
 public interface ISettings extends IConf {
+    String DEBUG_FLAG_NAMESPACE = "net.essentialsx";
+
     File getConfigFile();
 
     boolean areSignsDisabled();
@@ -141,6 +144,10 @@ public interface ISettings extends IConf {
 
     boolean isDebug();
 
+    boolean isDebug(DebugFlag flag);
+
+    Long getDebugLong(DebugFlag flag);
+
     void setDebug(boolean debug);
 
     boolean isEcoDisabled();
@@ -416,4 +423,52 @@ enum TeleportWhenFreePolicy {
         OFF
     }
 
+    // TODO: consider separating out non-bool values? or replace this with an object-mapped class?
+    enum DebugFlag {
+        GENERIC("debug.generic", true),
+        USERMAP_PRINT_STACK("usermap.print-stack", false),
+        USERMAP_MAX_WARNS("usermap.max-warns", false),
+        ;
+
+        private final String flagKey;
+        private final boolean isSetByGlobal;
+
+        DebugFlag(final String flagKey, final boolean isSetByGlobal) {
+            this.flagKey = flagKey;
+            this.isSetByGlobal = isSetByGlobal;
+        }
+
+        public String getFlagKey() {
+            return flagKey;
+        }
+
+        public boolean isSetByGlobal() {
+            return isSetByGlobal;
+        }
+
+        public String getSystemPropertyKey() {
+            return DEBUG_FLAG_NAMESPACE + "." + flagKey;
+        }
+
+        public String getConfigKey() {
+            return "debug." + (flagKey.replace("debug.", ""));
+        }
+
+        public String getSystemPropertyValue() {
+            return System.getProperty(getSystemPropertyKey(), "false");
+        }
+
+        public boolean getSystemPropertyBoolean() {
+            return Boolean.parseBoolean(getSystemPropertyValue());
+        }
+
+        public Long getSystemPropertyLong() {
+            final String value = getSystemPropertyValue();
+            if (NumberUtil.isLong(value)) {
+                return Long.parseLong(value);
+            }
+            return null;
+        }
+    }
+
 }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Settings.java b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
index c0b1c618245..3d02712d893 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Settings.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
@@ -855,12 +855,41 @@ public boolean warnOnBuildDisallow() {
     }
 
     private boolean _isDebug() {
-        return config.getBoolean("debug", false);
+        if (config.isBoolean("debug")) {
+            return config.getBoolean("debug", false);
+        }
+
+        if (config.isBoolean("debug.enabled")) {
+            return config.getBoolean("debug.enabled", false);
+        }
+
+        return false;
     }
 
     @Override
     public boolean isDebug() {
-        return debug || configDebug;
+        return isDebug(DebugFlag.GENERIC);
+    }
+
+    @Override
+    public boolean isDebug(DebugFlag flag) {
+        if (flag.isSetByGlobal() && (debug || configDebug)) {
+            return true;
+        }
+        final String flagConfigPath = flag.getConfigKey();
+        if (config.isBoolean(flagConfigPath)) {
+            return config.getBoolean(flagConfigPath, false);
+        }
+        return flag.getSystemPropertyBoolean();
+    }
+
+    @Override
+    public Long getDebugLong(DebugFlag flag) {
+        final String flagConfigPath = flag.getConfigKey();
+        if (config.hasProperty(flagConfigPath)) {
+            return config.getLong(flagConfigPath, 0);
+        }
+        return flag.getSystemPropertyLong();
     }
 
     @Override
diff --git a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
index eaab42c0f87..62330044859 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
@@ -1,8 +1,8 @@
 package com.earth2me.essentials.userstorage;
 
+import com.earth2me.essentials.ISettings;
 import com.earth2me.essentials.OfflinePlayer;
 import com.earth2me.essentials.User;
-import com.earth2me.essentials.utils.NumberUtil;
 import com.google.common.cache.CacheBuilder;
 import com.google.common.cache.CacheLoader;
 import com.google.common.cache.LoadingCache;
@@ -36,13 +36,13 @@ public ModernUserMap(final IEssentials ess) {
                 .softValues()
                 .build(this);
 
-        // -Dnet.essentialsx.usermap.print-stack=true
-        final String printStackProperty = System.getProperty("net.essentialsx.usermap.print-stack", "false");
         // -Dnet.essentialsx.usermap.max-warns=20
-        final String maxWarnProperty = System.getProperty("net.essentialsx.usermap.max-warns", "100");
+        final Long maxWarnSetting = ess.getSettings().getDebugLong(ISettings.DebugFlag.USERMAP_MAX_WARNS);
+        this.debugMaxWarnsPerType = maxWarnSetting != null ? maxWarnSetting : -1;
+
+        // -Dnet.essentialsx.usermap.print-stack=true
+        this.debugPrintStackWithWarn = ess.getSettings().isDebug(ISettings.DebugFlag.USERMAP_PRINT_STACK);
 
-        this.debugMaxWarnsPerType = NumberUtil.isLong(maxWarnProperty) ? Long.parseLong(maxWarnProperty) : -1;
-        this.debugPrintStackWithWarn = Boolean.parseBoolean(printStackProperty);
         this.debugNonPlayerWarnCounts = new ConcurrentHashMap<>();
     }
 
diff --git a/build-logic/src/main/kotlin/constants.kt b/build-logic/src/main/kotlin/constants.kt
index 5aebfc557a3..5cc2ea1602e 100644
--- a/build-logic/src/main/kotlin/constants.kt
+++ b/build-logic/src/main/kotlin/constants.kt
@@ -1 +1 @@
-const val RUN_PAPER_MINECRAFT_VERSION = "1.19.2"
+const val RUN_PAPER_MINECRAFT_VERSION = "1.19.3"